Crossdressing Sex: A Woman and a Crossdresser

Crossdressing Sex: What Goes On in the Bedroom?

The short answer: a lot. Adding the element of crossdressing into vanilla sex dramatically increases the number of sexual acts and scenarios and chances for pleasure. This essay explores the most common scenarios for the fully dressed crossdresser and her heterosexual female partner. The scenarios coincide with the most common types of crossdressers: the vanilla crossdresser who loves all things feminine and sensuous, including Women; submissive crossdressing men who loves all things feminine and sensual, including Women – their superiors; the submissive chaste crossdresser; and submissive crossdressers who seeks humiliation and see cross dressing as another avenue of sexual humiliation.

The Vanilla Sensual Crossdresser

Sensuality and crossdressing go hand in hand for many crossdressers.

More often than not, the crossdresser keeps on most of her lingerie throughout the sexual act. This includes the shoes. Their female partner is more likely to keep at least part of her own lingerie on, to both parties delight. Lingerie is exquisite to look at and to wear but too often in vanilla scenes lingerie is on view for seconds before being discarded. Many Women report sex with crossdressers as the most sensual sex act they’ve ever experienced. Women remark upon the care given to sensation: stroking one another becomes a wave of pleasure for both parties. Lingerie becomes part of oral sex and not an impediment. Before there was only mouth to skin contact, now there’s also mouth to fabric contact. The texture of the fabric adds layers of sensation to an already pleasurable act. If there is penetration from behind, it is usually the Woman in the dominant position, pleasuring her crossdresser anally. Sometimes she wears a strap-on; sometimes she uses her fingers to penetrate the crossdresser. Otherwise, missionary and cowgirl are the sexual positions of choice. Some vanilla crossdressing couples wear crotch-less panties so no clothes are removed during penetration.

The Submissive Sensual Crossdresser

Again, the clothes stay on. Unlike the vanilla crossdresser, the submissive crossdresser typically has her clothes chosen by her partner. The submissive crossdresser is fully dressed as a glamour puss: lacy bra, frilly underwear, strappy garters, high heeled shoes, sheer stockings, and in many cases a sexy chemise or baby doll on top of all that. The submissive crossdresser is also more likely to be wearing artfully applied makeup, with particular attention paid to the lips.

The submissive crossdresser is rather adept at worshiping her partner’s body: in addition to oral sex, the crossdresser will spend as much time as her partner wishes kissing/licking/sucking any of her partner’s pleasurable spots. Cunnilingus lasting for hours is not unheard of. The pleasure is not one sided.

The submissive crossdresser derives pleasure from serving her partner (not necessarily Mistress — some dominant Women are uncomfortable with the title). Her partner will use a strap-on for anal play and/or supply toys for the crossdresser to use on herself to the amusement and pleasure of the Woman.

If there is penetration of the Woman, many couples have the submissive crossdresser is in the bottom position with the Woman in the dominant, top position. Typically, penetration of the female does not occur until her crossdresser has undergone stamina training. As with the other sexual acts in the bedroom, penetration is for the Woman’s pleasure first and foremost.

The Submissive Chaste Crossdresser

Many couples find a submissive, chaste, and well-dressed crossdresser exhilarating. Women find a chaste crossdressing partner especially freeing. There is an ingrained assumption that sex is over once the shudders from orgasm have retreated. When the crossdresser is restrained, the Woman does not have to monitor her crossdresser for over-stimulation.

No matter how wonderful the crossdresser may feel, orgasm is denied to her and the scene goes on. What relief she may find from over-stimulation (or the chance for a sexual release) is at the whim of her partner. Knowing she can do nothing about her own pleasure she is completely dedicated to her partner’s.

Again, penetration can be part of the sexual acts. If the Woman is wearing a strap-on, she’ll gauge how much stimulation she can give her crossdresser without causing orgasm. Also, her crossdresser may have to orally worship the strap-on. Some Women enjoy having their vagina licked at the same time. The Woman can still be penetrated — the crossdresser will wear the strap-on this time. Usually the strap-on is different in size from the chaste crossdresser’s member. The number and occurrence of sexual positions is the same as in vanilla crossdresser sex.

Masturbation plays a large role in chaste crossdresser sex. As part of chastity training, some Women encourage their crossdresser to masturbate almost to the point of release, at which point she is denied orgasm and dons a chastity device. Both the submissive sensual crossdresser and the submissive chaste crossdresser can be given maid duties as a kind of foreplay; many Women direct their crossdresser to clean and arrange the house and herself several hours before the Woman enters the bedroom for sex.

The Submissive Humiliated Crossdresser

For this couple, dressing is seen as a humiliating punishment and the first of many. Many crossdressing cuckolds can be found in this group. Outsiders at first have a hard time understanding that though the crossdresser is humiliated by dressing up in female clothing and seen as a sissy, failed male, worthless man, etc, the Woman is still seen as all things dominant, wonderful, and worship-worthy.

For these kinky couples, sex might involve more BDSM acts. Most Women in these couples take other lovers. Some submissive crossdressers are encouraged to eat creampies, service their partner’s lover directly, or to watch (and perhaps help) as another man services their partner.

Crossdressers are a diverse group; and so are the sexual acts between a Woman and her crossdresser. This is just a brief glimpse into the types of sex crossdressing couples have. Women who have sex with crossdressers often echo some men’s appreciation of transsexuals: “It’s the best of both worlds. You can be touching a Woman, being with one and still have a warm-blooded cock to play with.”

Give on of our Feminization Mistresses a call today to discuss crossdressing sex and the various nuances and scenarios.